scholarly journals A Structural Analysis of the Angucycline-Like Antibiotic Auricin from Streptomyces lavendulae Subsp. Lavendulae CCM 3239 Revealed Its High Similarity to Griseusins

Antibiotics ◽  
2019 ◽  
Vol 8 (3) ◽  
pp. 102 ◽  
Author(s):  
Maria Matulova ◽  
Lubomira Feckova ◽  
Renata Novakova ◽  
Erik Mingyar ◽  
Dominika Csolleiova ◽  
...  

We previously identified the aur1 gene cluster in Streptomyces lavendulae subsp. lavendulae CCM 3239 (formerly Streptomyces aureofaciens CCM 3239), which is responsible for the production of the angucycline-like antibiotic auricin (1). Preliminary characterization of 1 revealed that it possesses an aminodeoxyhexose d-forosamine and is active against Gram-positive bacteria. Here we determined the structure of 1, finding that it possesses intriguing structural features, which distinguish it from other known angucyclines. In addition to d-forosamine, compound 1 also contains a unique, highly oxygenated aglycone similar to those of spiroketal pyranonaphthoquinones griseusins. Like several other griseusins, 1 also undergoes methanolysis and displays modest cytotoxicity against several human tumor cell lines. Moreover, the central core of the aur1 cluster is highly similar to the partial gris gene cluster responsible for the biosynthesis of griseusin A and B in both the nature of the encoded proteins and the gene organization.

2009 ◽  
Vol 8 (2) ◽  
pp. 324-332 ◽  
Author(s):  
Matthew S. Squires ◽  
Ruth E. Feltell ◽  
Nicola G. Wallis ◽  
E. Jonathan Lewis ◽  
Donna-Michelle Smith ◽  
...  

1999 ◽  
Vol 44 (3) ◽  
pp. 235-240 ◽  
Author(s):  
Michael J. Kelner ◽  
Trevor C. McMorris ◽  
Mark A. Montoya ◽  
Leita Estes ◽  
Sheldon F. Uglik ◽  
...  

2013 ◽  
Vol 2013 ◽  
pp. 1-12 ◽  
Author(s):  
Wilfredo Hernández ◽  
Juan Paz ◽  
Fernando Carrasco ◽  
Abraham Vaisberg ◽  
Evgenia Spodine ◽  
...  

The palladium(II) bis-chelate complexes of the type [Pd(TSC1-5)2] (6–10), with their corresponding ligands 4-phenyl-1-(acetone)-thiosemicarbazone, HTSC1(1), 4-phenyl-1-(2′-chloro-benzaldehyde)-thiosemicarbazone, HTSC2(2), 4-phenyl-1-(3′-hydroxy-benzaldehyde)-thiosemicarbazone, HTSC3(3), 4-phenyl-1-(2′-naphthaldehyde)-thiosemicarbazone, HTSC4(4), and 4-phenyl-1-(1′-nitro-2′-naphthaldehyde)-thiosemicarbazone, HTSC5(5), were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and1H- and13C-NMR). The molecular structure of HTSC3, HTSC4, and [Pd(TSC1)2] (6) have been determined by single crystal X-ray crystallography. Complex6shows a square planar geometry with two deprotonated ligands coordinated toPdIIthrough the azomethine nitrogen and thione sulfur atoms in acisarrangement. Thein vitrocytotoxic activity measurements indicate that the palladium(II) complexes (IC50=0.01–9.87 μM) exhibited higher antiproliferative activity than their free ligands (IC50=23.48–70.86 and >250 μM) against different types of human tumor cell lines. Among all the studied palladium(II) complexes, the [Pd(TSC3)2] (8) complex exhibited high antitumor activity on the DU145 prostate carcinoma and K562 chronic myelogenous leukemia cells, with low values of the inhibitory concentration (0.01 and 0.02 μM, resp.).Corrigendum to “Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines”


Oncology ◽  
2006 ◽  
Vol 71 (1-2) ◽  
pp. 86-94 ◽  
Author(s):  
Gregory J. Wirth ◽  
Kathrin Schandelmaier ◽  
Victoria Smith ◽  
Angelika M. Burger ◽  
Heinz-Herbert Fiebig

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